Some Nights I Stay Up Cashing in My Bad Luck
by SliverTonguedHunter
Summary: Dean Winchester never thought that he would be falling in love with his best friend, Castiel Novak. He never thought that they could be something more than best friends. He could never picture holding his hand or kissing him goodnight. Dean Winchester never planed on falling in love with his best friend, but that doesn't mean that he wasn't happy it was happening. AU oneshot


The first time Dean Winchester met Castiel Novak was when they were five years old. He was playing outside his house, pretending that there was a battlefield and that he was the only soldier left. Dean ran across his front yard, making sound effects and throwing sticks to represent weapons. He was looking behind him when he ran straight into Castiel. They toppled to the ground, scrapping their knees and rolling in the dirt as they tried to separate. That was the first time Dean saw Cas' blues eyes and it wasn't the last time he would get lost in them. They muttered apologies and Dean couldn't help but laugh. The boy in front of him was dressed in a now filthy suit. The tie he was wearing was now hanging loosely and his white shirt was untucked with patches of dirt all over it. Cas' black hair was sticking out all over the place and he had a confused look on his face. Dean only laughed harder. He stuck his hand out and gave Cas a toothy grin. He said his name and Cas returned the gesture. Thus, their friendship began.

They began to hang out all the time. Turns out that Cas' family just moved in across the street and that Cas was the same age as Dean. Sam was eager to have friends in the neighborhood and got along great with Cas' brother, Gabriel. Whenever Cas needed a hand, Dean was there to pick him up. Whenever Dean would get into fights, Cas would be right behind him, throwing punches also. They were joined at the hip.

The first time Dean was ever kissed was by Lisa, a girl who had a crush on Dean for as long as he could remember. It was during her 14th birthday party when someone suggested to play spin the bottle. It landed on him and he was more than eager to comply. Dean went home that night happier than ever, smiling like an idiot. Cas showed up less than five minutes later, frowning as he struggled to sneak into Dean's room without making any noise. Dean's smile only got bigger. He explained the kiss to Cas in full detail, getting more and more excited by the minute. Dean told Cas that he wanted to practice more but had no one to practice with. Cas only blushed and said he'd be willing to do it. The first time Castiel received his first kiss was with his best friend, Dean. This wasn't the last time too.

In tenth grade, Dean realized that he was bisexual. It was completely by accident too. He tried to deny it all he wanted but he couldn't help but notice his best friend, Castiel. He didn't talk to Cas for a week after that. He started to go out with all the girls he could, landing him a track record in school. His grades started to drop and he began to skip class whenever he felt like it. Cas got worried and cornered Dean, pressuring him into telling him what's wrong. Dean only pushed past him and left. Cas didn't see him until one week later during finals. They didn't speak the entire summer. When eleventh grade came around, Dean avoided Cas for as long as possible until Meg and Gabriel kidnapped Dean and shoved him into Cas' room. They talked all night and Dean finally admitted to Cas what he was feeling. Cas only responded with pressing his lips against Dean's. Cas knew that all was well again.

The first time Dean heard the phrase "I love you" was by Cas during their three month anniversary. It happened quickly and Cas turned bright red afterwards. He didn't mean for it to come out. They were sitting in Cas' room, listening to Metallica, a band that Dean forced Cas to listen to and fall in love with. Dean had been playing with Cas' hair, twirling it around his fingers while Cas tried not to lose focus on his homework. Dean began to kiss Cas' neck, hoping to distract him long enough to at least get in a make out session. Cas groaned, placing down his pencil and moving his neck so Dean could have more room. He began to suck on Cas' neck when the words just came out in a pant. Dean stopped kissing, but Cas could feel the smile on his kiss. Dean's reply was muffled against his skin but Cas turned bright red, heat radiating off of his skin. Cas fell asleep smiling that night.

The first time they got into a fight was only two weeks later. They had been in the hallway at school, holding hands and walking to class when a jock made a comment about them. Dean got mad and threw the first punch, ending with him getting a one week suspension. Cas told Dean to let it go and that people will always be commenting on their nature. This only made him even madder. Cas looked hurt, staring in disbelief at Dean as he paced back and forth, yelling. Cas didn't say a word. He let Dean continue on, the knot in his stomach worsening with every step. Cas went home in tears. He didn't respond to Dean's calls or texts.

Cas didn't want to return home that night. He merely got in his car and continued to drive until he was tired. Tears spilled out of his eyes. His voice cracked when Anna called him, begging him to come home. Cas replied with a "no" and turned off his phone. He didn't see the other car swerving into his lane until it was too late. The only think he saw was a flash of bright, white lights and Dean's voice ringing in his ears.

This wasn't the first time Dean has felt utter despair. When Dean was four, his mother died in a house fire. He carried Sam out of the house and watched it burn to the ground. When Dean was sixteen, his father died from alcohol poisoning. They moved in with their Uncle Bobby two days after the funeral. So when Dean got the news that Cas was in critical condition, he knew what the feeling was in the pit of his stomach. He rushed to the hospital, Sam following along with him. The second he saw Cas, he felt bile coming up his throat. He tugged on his jacket, pulling the worn away leather against his body as tightly as it could go. Sam pushed him towards the door to the room. Dean refused to enter, staring into the room's window. Cas was hooked up to at least six machines, a breathing tube hooked into his nose and an IV placed into his arm. His face was bruising and there were cuts covering his body. Dean didn't stay that day. He went home and didn't return for another two days.

When Dean finally visited Cas, he was awake and able to talk. They didn't speak though. Dean just sat down in a chair next to Cas' bed and buried his head in his hands. Cas patted his head, coughing in the process. Dean grabbed Cas' hand, examining it as if it was the most fascinating thing in the world. His hands were pale white, well paler than usual. Tears spilled out of Dean's eyes, cupping Cas' hand and holding it against his forehead. He tried to sputter out an apology, saying that it was his entire fault. Cas smiled weakly, accepting Dean's apology. Dean didn't leave his bedside not once the entire time. He didn't even go to school until he knew that Cas would be in class with him.

When Cas was finally released from the hospital, Dean changed. He became more overprotective, never truly leaving him alone. He held Cas' hand and refused to let go. He spent every day at Cas' house, always cooking and comforting. He changed Cas' dressings on his cuts. He wrapped his ribs when they began to hurt. He helped him to get dressed and kissed every wound he could see. Michael and Lucifer, Castiel's older brothers, hated how Dean acted towards Cas. They didn't like how he babied their youngest brother or how Cas had forgiven Dean so quickly. Anna and Gabriel thought it was precious and adorable how Cas was being treated. Cas only blushed.

By the end of twelfth grade, Dean Winchester and Castiel Novak were madly in love and ready to take on the world together. Graduation came and went, then the summer and soon came August. Dean was staying behind for at least year, to work at Bobby's auto shop so he can raise money for college while Cas was accepted to some school across the country. Cas told him that he could put off a year so that he could see Dean more but Dean refused the offer. They promised each other to visit as soon as possible, but the promises soon fell flat. Dean worked every day and Cas got lost in the magic of college. He studied all the time, never truly sleeping unless he reached his max. Dean began taking classes at the community college so that he wouldn't fall behind. They stopped calling and texting each other every day. Soon, they didn't even talk at all.

Cas cheated on Dean with a man named Balthazar after about 2 months of not talking to Dean. He felt lonely, abandoned by him. They had sex after getting hammered at a bar. Cas regretted it and felt sick to his stomach. All he could picture was his life with Dean and the future they held. He told Dean what happened hours after. Dean refused to talk to him for the rest of the week. Dean retaliated by sleeping with a different woman each day of the week. They broke up once Dean told him what he did.

Thanksgiving passed and then Christmas. Sam noticed how heartbroken Dean was and Gabriel gave daily checkups on how Cas was doing to Sam. So Sam and Gabriel came up with a scheme to get them back together. They lied to Dean and Cas, saying that they had gotten into a car accident while heading towards a movie that night. Cas came rushing home from Yale and Dean took the next two days off from the shop. Gabriel and Sam told them to meet them at the house and that they had been released from the hospital. They locked them in a room for the entire night. All that could be heard was screaming and smashing for half of the night. Sam assumed that it was going to take longer than they thought.

Dean threw a photo of them against the wall, the glass smashing and falling to the ground. Cas yelled right back, his hands clenching and unclenching with every word. He shoved Dean, pushing him against his desk. Dean pushed straight back, shoving Cas onto the bed. He pulled Dean down with him, pressing his lips furiously against Dean's. Dean's arms held him up the bed, his hips clashing with Cas'. Cas shuttered underneath and moaned. His hands pushed up Dean's shirt, his fingers lightly tracing out his abs. Their lips fought one another, biting and tugging. Soon both shirts were tossed somewhere in the room, their bodies tangling with one another. They broke away panting, their lips swelling and turning red. Dean pushed Cas away for a minute, swallowing breath after breath in hopes of calming down. They looked at one another. Cas smiled and Dean only laughed. All was forgiven. Cas only rolled back on top of Dean and their kissing continued.

When Cas finally turned twenty one, Dean took him out to celebrate. Now Cas had gotten drunk before, multiple times before on Dean's behalf. They have gone to parties and gotten wasted. But this time was different. They could do it without the fear of getting caught. So when they spilled back into Cas' dorm room, laughing hysterically, Dean asked Cas to marry him. Cas only smiled and took the ring from Dean's fingers and put it on his own.

**Author's Note: So this is my first time writing for Supernatural even though I love it dearly. Obviously it is AU and obviously, I do not own the show. If I did however, Cas and Dean would be together already. I hope you have enjoyed this oneshot. Look for a new story coming from me soon about them! For now, stay safe. Use salt. **


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